Of all the secrets nurtured by John F. Kennedy, his life-long love affair with another man was arguably the most risky.
Kirk LeMoyne Billings, who went by Lem, was 16 years old when he first met Jack Kennedy, then 15.
It was the fall of 1933. Both were enrolled at Choate, an elite all-boys boarding school in Connecticut.
For Lem, it was practically love at first sight. Jack Kennedy was everything he was not: roguish, charismatic, confident, effortlessly popular — not just with other students, but girls and women.
In the beginning, at least, Jack didn’t realize that Lem harbored romantic feelings for him.
But at some point in their friendship, Lem confessed his desires to Jack in a message scrawled on toilet paper — a common trick at Choate, so that boys could easily swallow or destroy love notes to each other.
That note has been lost to history, but Jack’s written response was not.
‘Please don’t write to me on toilet paper anymore,’ Kennedy replied. ‘I’m not that kind of boy.’

John F. Kennedy and Kirk LeMoyne ‘Lem’ Billings are pictured reclining in a wicker lounge chair outside the Kennedy family home in Palm Beach, Florida in 1936.Â

Harry Dixon, Kathleen ‘Kick’ Kennedy, John Coleman, Charlotte McDonnell, Jack and Lem (wearing matching shorts) link arms in Palm Beach at Christmas time in 1940.

Jack and Lem sit aboard a boat off the coast of Hyannis Port, Massachusetts in July 1933, along with an unidentified girl.Â
The realization that his new best friend was gay, however, did not deter Kennedy from maintaining a deep friendship with Lem — quite remarkable for the mores of pre-World War II America, and indicative of Kennedy’s sophistication and maturity at a young age.
Jack did not worry that his peers or parents might think he, too, was gay. Perhaps the sexual perversion that infested the Kennedy family blunted that concern: Father, sons and brothers often shared the same women. Yet there was never any acknowledgment of the homoeroticism involved.
So Lem became a constant presence at the Kennedys’ famed compound on Cape Cod, and Jack’s forever shadow.
The narcissist in Jack loved the attention, the adoration, the hero-worship that Lem showered upon him.
Their classmate at Choate, Rip Horton, witnessed Lem’s complete servitude.
As Horton told Kennedy chronicler Nigel Hamilton for his 1992 biography of JFK: ‘In Lem, Jack found a slave for life. It was amazing how Lem was abused. He did Jack’s laundry. Late at night, he’d run out in the cold weather to buy a pizza. Jack’s back was always hurting’ — he would go on to have multiple spinal surgeries — ‘and Lem became his unpaid masseur, a job he relished.’
And, as Lem claimed later in life – after JFK was assassinated – he often gave Jack oral sex. They even had a shared nickname for Jack’s penis: J.J. Maher, apparently named after their strictest teacher at Choate.
Jack — an always sickly boy whose parents rarely hugged or kissed him, who was expected to excel at everything — found, in Lem, unconditional love and affection.
Yet a part of Kennedy seemed to remain in denial about Lem’s sexual orientation.
Among the voluminous correspondence between them — which Billings saved, despite Jack’s admonition, at the end of most missives, to ‘burn this letter’ — were graphic tales of sexual conquests and onanism.
In one note to Billings from 1934, sent during one of Jack’s many hospital stays, he lamented that he had only masturbated twice since being admitted: ‘My vitality is slowly being sapped… I’m just a shell of the former man and my penis looks as if it had been run through a ringer.’
In another, Jack joked: ‘The nurses are very tantalizing and I’m really the pet of the hospital… [the] nurses are almost as dirty as you, you filthy minded s**t.’
Upon his return to Choate, he wrote again to Lem: ‘I still have your shaving brush, which I shall return once I get my deer-Sucker coat you slimy f***. Have you laid p***y yet? You bitch.’
Such insults were part of Jack’s love language, and Billings took them as such. When Jack came up with the idea that they should lose their virginity together — Jack, again, perhaps willfully oblivious to the intrinsic homoeroticism — Billings went along.
Off they travelled, from Choate, to a brothel in New York City. Jack insisted they should share the same prostitute.

Jack and Lem play in the snow at Choate, an elite all-boys boarding school in Wallingford, Connecticut that they both attended.Â

Jack and Lem pose with the nanny to the Kennedy children – Katherine Conboy – outside of their family home in Palm Beach, Florida.Â
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Jack and Lem (right) outside a drugstore in the mid-1930s.Â
Whether they shared this sexual encounter as a threesome remains unclear, but their friend Rip Horton later said that ‘Billings and Jack came back in a terrible panic because of [venereal disease]. They went to a hospital and got all these medicines and creams.’
As a taunt or a tease, and even while flirting heavily with Lem, Jack often wondered aloud why Billings couldn’t find a suitable girlfriend.
In a letter sent during his brief stint at Princeton University, Jack wrote to Lem: ‘I don’t know why you […] are so unpopular with girls… You’re certainly not ugly looking exactly… I guess you are just not cut out to be a ladies man.’
Jack’s scrapbook from Choate, housed at his presidential library in Boston, is full of photos of Lem, or the two of them together — one with Lem posing upside down, his backside facing the camera, between Jack’s legs.
Another has Lem hoisting young Jack up by his backside, with loving messages scrawled alongside.
Next to one of Lem: ‘A pretty sight! Woof – woof.’
Another, also of Lem: ‘What a kisser.’
In the summer of 1936, one year after graduating from Choate, Jack wrote to Lem from Los Angeles of a groin injury that would hinder intimacy between them: ‘If you could see what a thing of beauty my body has become with open air… It looks as though there will be no little rascals bearing the name LeMoyne Kennedy as yesterday I got kicked where I love, which stretched me out for a few blissful minutes… I have not heard from you for 3 weeks except for a couple of smutty postcards… Please communicate.’
Lem, of course, would never leave Jack. Not even when a beautiful young debutante named Jacqueline Bouvier entered the picture.
Early in their courtship, which began in 1952, Jackie knew two things: She wanted to marry Jack Kennedy, and that meant accepting Lem Billings and entering a love triangle.
Lem was, for Jack, non-negotiable.Â
Did Jackie know that her future husband had been intimate with Lem? That Jack and Lem joked about having a child together? That on a two-and-a-half month European trip they took together in 1937, they had jointly purchased a Dachshund that they named Dunker — a dog they quickly had to re-home due to Jack’s allergies?
If so, she never said a thing.
Nor did she blanch when Jack’s friend Langdon Marvin, the godson of President Franklin D. Roosevelt, told her one night that if Jack were to marry her, it was only ‘because people are starting to call him a ‘fairy’. In this country, if you’re not married by 40, you’re suspect.’
Jackie, however, had a gift for reading people. She quickly realized that Lem and Marvin were both in love with Jack and trying to scare her off.
In September 1953, she and Jack wed in a lavish ceremony in Rhode Island. By 1960, they were in the White House — and so was Lem, with his own bedroom in the private residence.
Jackie confessed to Senator George Smathers, one of JFK’s closest allies, that she could barely stand it.
‘Just one weekend in my life,’ she said, ‘I’d like to have my husband to myself. But Lem is always there, bathing and massaging him, even putting on his shoes and socks.’
Whispers about JFK and Lem’s ‘special relationship’ flew through DC, the press corps, the FBI and CIA — the latter agency worrying that Russia and other enemy states could blackmail the president with such information.
Jackie understood. Her own father, ‘Black Jack’ Bouvier, was a womanizing bisexual. Very little shocked her, and she came to appreciate Lem’s loyalty and discretion, the ‘stress relief’, as Lem often put it, that he provided for Jack.
But he wasn’t always so quiet about it.

A photograph of Lem hoisting Jack up by his backside on campus from Jack’s Choate scrapbook, along with the scribbled caption, ‘Don’t be so personal, LeMoyne’.

On a two-and-a-half month European trip they took together in 1937, Jack and Lem jointly purchased a Dachshund that they named Dunker, a dog they quickly had to re-home due to Jack’s allergies.

Jack and Lem are pictured in uniform in Palm Beach in 1944 – one year before the end of World War II.Â

Jackie Kennedy holds son JFK Jr. as she rides in a golf cart along with Jack and Lem (right) in Atoka, Oklahoma in 1963.Â
Billings later told his close friend, Hollywood journalist Lawrence J. Quirk, that he and Jack had been intimate, and that it was ongoing, with Lem providing oral gratification to Jack — never the other way around.
Billings, Quirk said, ‘believed that this arrangement enabled Jack to sustain his self-delusion that straight men who received oral sex from other males were really only straights looking for sexual release.’
That never bothered Billings.
‘People think I’m a joke,’ he once said. ‘But I’m stuck with the Kennedys emotionally, and I will be to the end of my life.’
The mutual devotion Jackie and Lem had for JFK did little to soften their relationship.
‘There was no great love between them,’ Washington correspondent Charlie Bartlett said. ‘They were rivals for Jack’s love. Poor Lem was always the third person at what Jackie hoped would be an intimate dinner with her husband. Apparently, Lem never heard the expression ‘three’s a crowd’, but Jack insisted Lem be there. I don’t think Lem ever really liked Jackie, but he did come to respect her. He felt she was more a great mother than a wonderful wife.’
Meddlesome Langdon Marvin was far easier to dispatch with — in fact, he did it to himself.
After running into famed author Gore Vidal – himself related to Jackie by marriage and openly gay – Marvin revealed what caused his expulsion from the Kennedy inner circle: ‘Year after year, I broke my balls for Jack, and this is how I’m treated. My crime? One night I lost control and did what I’ve always wanted to do to him. I couldn’t help myself… Apparently, he allows Lem to do the unspeakable, but he treated me like s**t.’
Marvin had been done a favor.
For when JFK was assassinated in 1963, it was Lem who would never recover, never move past it, never build a life for himself outside of Jack and the Kennedys.
‘Jack made a big difference in my life,’ Billings later said. ‘Because of him, I was never lonely. He may have been the reason I never married.’
Years later, Billings would find himself a new Kennedy obsession: Robert F. Kennedy Jr., troubled and adrift after his own father was assassinated in 1968 while running for president.
Bobby Jr.’s mother Ethel, who had been left to raise eleven children, sent her troublesome son to live with Billings. He was 14.
Billings became the primary adult in Bobby Jr.’s life: overseeing his education at New York’s Millbrook boarding school, taking him on vacations, and ultimately claiming to have shared drugs with him.
Millbrook teacher James Hejduk told RFK Jr.’s biographer Jerry Oppenheimer that Lem was a constant presence, and that the faculty had been told he was Bobby’s surrogate father.
‘He was coming up and taking Bobby out to dinner and things like that,’ Hejduk said. ‘Of course, that gave most of us the thought — does this guy have a job other than caring for Bobby?’
Mark Bontecou, part of one of the richest families in Millbrook, was more alarmed. ‘The one thing that struck me,’ he said, ‘even at that tender age, was that I felt Lem was just obsessed with Bobby — the way he watched over him, the way he was hugely protective of him.’
Jackie, who had relocated to New York after JFK’s death, was sure to keep her children, John Jr. especially, away from Billings.
But Ethel Kennedy, it seems, had all but abandoned her son to this most desperate Kennedy groupie, who would do anything to cleave to an alpha heir.
When Bobby began doing heroin at age 15, Billings, rather than intervene, claimed to have joined him.

Jack and Lem are pictured together in April 1962 in the White House.

Lem and Jack are pictured here in Hyannis Port in 1959 with an unidentified friend.Â

Billings found himself a new Kennedy obsession after Jack’s assassination: Robert F. Kennedy Jr. (middle), troubled and adrift after his own father was assassinated in 1968 while running for president. Lem (left) is pictured here with RFK Jr and his mother Ethel Kennedy (right).Â
When he and Bobby would visit Ethel at Hickory Hill, her Virginia family home, they would sit at the dining table in matching bathrobes and drink alcohol — straight shots — at 8.30 am.
As with JFK and Jackie, Billings attempted to insert himself into young Bobby’s love life: telling Bobby that he needed to marry a woman like his aunt Jackie, and using one of Bobby’s girlfriends, a Staten Islander named Valerie Duff Pacifico, as a confidante.
Billings, Pacifico said, would at times be ‘close to tears’ during phone calls with her, asking her if she thought ‘Bobby loved him’.
Bobby, by this point, was in his early twenties, and Billings was trying to break him and Pacifico up — telling Bobby that she wasn’t a suitable Kennedy wife.
No woman would have been a suitable Kennedy wife to Billings. He was, as biographer Sally Bedell Smith so memorably put it, ‘probably the saddest of the Kennedy widows.’
He was also the most consumed by rage.
‘Billings had a real streak of cruelty and abuse in him,’ another Kennedy biographer, David Horowitz, said. ‘Here’s the guy who’s supposed to be the father figure and he’s… doing heroin with Bobby and shooting delusions up his ass that he would be president one day.’
As Bobby Jr. went away to Harvard and began forging his own life, Billings fell further into drug and alcohol abuse.
On the day before he died in May 1981, Billings was inconsolable after Bobby had cancelled a trip the two had planned to Haiti.
‘You’ve got to take care of Bobby,’ Billings told Harvey Blake Fleetwood, another inner-circle hanger-on.
Fleetwood replied that he didn’t need to, because Billings would always be there.
Billings began to cry. ‘No,’ he said. ‘I made a terrible mistake. I took drugs with him. I made a terrible mistake. I let him down.’
The next night, Billings died in his sleep at age 65. The cause was a heart attack, but it may as well have been a broken heart.
JFK’s sister, Eunice, delivered Lem’s eulogy.
‘I’m sure he’s already organizing everything in Heaven so it will be completely ready for us,’ she said, ‘with just the right Early American furniture, the right curtains, the right rugs, the right paintings.’
That was Lem to the Kennedys: even in death, only and ever their faithful servant.